The spirocyclopropyl moiety as a methyl surrogate in the structure of L-fucosidase and L-rhamnosidase inhibitors

Nitrogen-in-the-ring analogues of L-fucose and L-rhamnose were prepared, which feature a spirocyclopropyl moiety in place of the methyl group of the natural sugar. The synthetic route involved a titanium-mediated aminocyclopropanation of a glycononitrile as the key step. Four new spirocyclopropyl iminosugar analogues were generated, which displayed some activity towards L-fucosidase and L-rhamnosidase. (c) 2009 Elsevier Ltd. All rights reserved.


Published in:
Bioorganic & Medicinal Chemistry, 17, 8020-8026
Year:
2009
Keywords:
Laboratories:




 Record created 2010-11-30, last modified 2018-03-17


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